The Three Gigolos Ch. 02

I could hardly sleep thinking about meeting Tanya's sister Janet and the possible threesome that could result. I tried to visualize how it would go, but then thought I'd be better off just letting Uncle Vince's orchestrate it as he had done with Tanya. He's the one that really understood Janet and would know how to make it good for all of us. I had been an amazing time with Tanya, and I was now being trusted by my favorite uncle to take his place as her "special" home delivery guy. If all went well, I would also be the "special delivery guy" for her sister. I could only hope Janet would be as attractive and sexy as Tanya.

Just as the day before, we made several deliveries to clear the schedule before going to Janet's house. She lived in a distinctly different neighborhood than did Tanya. Tanya's house was a vintage two-story house in an older part of town and was situated on a street with similar houses on small lots. There was perhaps only 10-12 feet between houses. On the other hand, Janet lived in a medium-sized one-story ranch style house in a newer neighborhood. It certainly wasn't an upper-class area like out in "The Valley", but it was apparent that the occupants had somewhat higher incomes. Janet indeed had her own car and didn't really require the grocery delivery service. Her choice for home delivery was obviously not just for groceries. She was more interested in Vince's "meat" rather than anything she could buy at my grandfather's store. OK, bad pun.

Vince used a driveway alongside the house to a back yard where he parked the truck next to a garage. Various bushes and trees helped to screen any view of the truck from the street as well as from neighbors. While I held the box of groceries, Vince knocked. Like yesterday, the door swung open quickly. As with Tanya the day before, Janet looked a bit befuddled to see me along with Vince. She said nothing but quickly motioned us inside. It was easy to see that Janet and Tanya were sisters. They had similar faces and bodies. I learned later that Janet was about two years younger than Tanya and had just turned 40. Her form-fitting jeans and simple tee shirt hinted that there was quite a nice body beneath them.

"Imagine my surprise that you're not alone," Janet said. "Who's your assistant? Please don't tell me you're getting too weak to carry a box on your own."

Once again Vince introduced me as his nephew who was recently out of the Navy and working part time for the store until he decided on a more permanent course for life. This time, however, we didn't go through all the shenanigans of me taking off my shirt and pants and such. Vince must have known that a more direct approach would work best. I recalled how yesterday he had told me that his start with Janet had been rather simple and straightforward because of her prior discussions with Tanya. There had been no need for a lot of preliminary flirting and uncertainty.

"I brought Nick along," Vince said, "because I knew it was a perfect opportunity to explore some of your secret little desires we often simulate. I thought it was a perfect time for you to enjoy the real deal."

I must have looked a bit puzzled. Vince had mentioned something about Janet's "little kinks" but hadn't given me the details...yet.

Vince continued, "Nick and I were at Tanya's yesterday to have a bit of three-way adventure with her. I knew it would be perfect to bring him over today so that you could meet him, and we could share some of the interesting activities we've talked about."

"Wait," Janet said. "You guys were at my sister's yesterday and she didn't tell me? You gave her first crack at this hunky nephew of yours, and she didn't call me? That sneaky little...I won't say the word. Wait till I talk to her. Jesus. She's keeping secrets from me now?"

Vince was laughing because he knew that Janet wasn't really that upset. "It's not her fault. She wanted to call you and I begged her not to. I wanted to surprise you the same way we did her."

"OK," Janet responded. "Consider me surprised, but she's still in trouble for not calling me with the juicy details."

I was still a tad confused as to what was supposed to happen with Janet other than a similar threesome we had with Tanya. Vince cleared that up immediately.

"So, Nicky," Vince explained to me. "Janet has a bit of a fetish for sometimes wanting to have backdoor intercourse. She enjoys a bit of anal play. You understand, right?"

Janet interjected. "To put it more bluntly, what your uncle is saying is that I sometimes like getting fucked in the ass."

"Right," Vince added addressing me. "But it's even a tad more interesting. As with Tanya, I showed Janet some of my smoker films where there were double penetration scenes. If that isn't obvious to you, it's when a woman takes it in the pussy and ass at the same time from two men. We've role played it with some nice cucumbers in my delivery box or with some of Janet's dildoes she uses for her private pleasure time. I'd have my rod in her pussy while working a dildo in her ass or I'd be in her ass and she'd be worked a cucumber or zucchini in her cunt. Stuff like that. It's not an every-time thing, but sometimes she's in the mood for both holes getting filled at the same time."

I remembered some of Uncle Vince's "smoker films". I had seen a few of these silent flicks that my friends had, but not any of Uncle Vince's until I asked him to show me some months later. Back in the "old days", 16mm one-reel porno films were called "smokers" because they were often shown in smoke-filled basements or backrooms of bars at "stag parties" where horny guys drank beer, smoked cigars, and watched hardcore fucking and sucking projected on bed sheets tacked to the wall. They started being available way back in the '20's and 30's when out of work actors and actresses did porn for a few bucks to pay the rent. Usually, they were shot in private homes with second-rate cameras and certainly didn't have studio production values. They were often out of focus with bad lighting and shaky cameras. They were basically illegal and bought "under the counter" or via backchannels from "a friend of a guy who knew a guy". Women very rarely saw them unless their husbands or boyfriends had some. Production quality got a bit better after the war, but pretty much disappeared in the 70's when "Deep Throat" started the "porno chic" movement. It was a whole new culture where ordinary couples went to X-rated theaters to see "adult films". However, it was the advent of inexpensive VCR's and videotape rental stores that brought porn into the homes of average suburban couples.

Janet looked at me and continued Vince's discussion. "When I first saw a woman simultaneously getting in in her pussy and ass, I was so fucking turned on. I tried it myself with two of my dildoes. At first it was a bit tricky, and I was a little timid. Gradually I got the hang of it, and the orgasms it gave me were true screamers. It just felt so amazingly erotic, dirty, and sinful. It's not something I'd tell most of my friends about. I told Vince about it, and he was more than ready to participate with his own tool filling one or the other of my holes while we used something else in which ever one was empty."

Vince jumped in and said, "We often talked about getting a second guy to make it real, but neither of us knew anyone we trusted enough. Then bingo, along came my special nephew Nick fresh from seeing the world in the Navy. After yesterday, I knew you'd be up for more adventure with my sweet but very naughty Janet."

"And," Janet said, "from what I see, I think Nick is indeed up for it as well."

She stepped over and kissed me while her hand went to my crotch.

"Ummm," she cooed. "Are you a baseball player, Nick? It sure feels like you brought your bat and balls along for a few innings of fun."

(OK, another really bad pun but I just couldn't help it.)

Janet went on, "Are you a nice guy, Nicky? Did they teach you that nice guys share their toys? Will you be a nice guy and share your bat and balls with me?"

As soon as she said it, she dropped to her knees, unbuckled and unzipped my pants, and dragged them to the floor. Before she pulled my briefs down, she put her face to them and breathed in deeply.

"Ummm, I love the smell of a horny man," she moaned. "Sniffing warn-in briefs does to me what sniffing worn-in panties does to the kind of guy I appreciate. How about you Nick? Do you love the smell and the taste of pussy?"

Before I could answer, she pulled my briefs down and began licking my balls and dick. After a few moments of giving my junk a nice tongue bath, she took my dick into her mouth and began a nice slow mouth fuck. I saw Vince taking his clothes off. When he was naked, he came over to turn Janet toward him so that she could transfer her blowjob talent to his cock.

"Finish taking your clothes off Nick," he said, "and then we'll take Janet back to her nice comfy bed to remove that tee shirt and jeans."

As soon as I got my clothes off, Vince lifted Janet up and carried her down the hall to her bedroom. She was giggling like crazy and making mock cries of being ravaged. It was easy to see that the thought of being carried off to get fucked by two men was the delight of her day.

Vince put her down on the bed and pulled off her jeans. She wore no panties under them. I helped her off with her tee shirt to see what I had suspected. She wore no bra over her beautiful breasts. Janet was perhaps a couple of pounds heavier than Tanya, but her body was outstanding. Like Tanya and most women of that time, she sported a full natural bush through which you could just make out her pussy lips. She reached up, pulled me to her face and kissed me deeply. At the same time, Vince held her ankles, spread and lifted her legs and plunged his face into her crotch. Vince licked and finger fucked her pussy while Janet and I continued to kiss. Then she looked up at me and said, "Fuck my mouth, Nick. Go ahead and use my mouth like a cunt."

I didn't have to be told twice. I put the two pillows under her head, straddled her chest, and guided my dick into her mouth. Her moans of pleasure from Vince's tongue vibrated her lips and mouth against my hard flesh. I could glance back to see Janet's legs wide open and my uncle working his tongue and fingers in and around her exposed womanhood. But then again, watching my cock slide in and out of her willing receptive mouth was even hotter. She seemed lost in the simultaneous sensations of tongue in pussy and cock in mouth. I really don't know how long it went on, but it was fantastic. I worked hard to not blow my load because I knew that this wasn't intended to be the end of the festivities.

In a few moments, Janet pushed me back and said, "Let me up so I can squat on your face. I heard you say you loved pussy Nick. Let's see how much. Do you love it as much as your uncle? He sure seemed happy munching my muff."

Vince backed off and Janet motioned for me to take her place lying back with my head on the pillows. She threw her leg over me, and straddled my face so that her crotch was right over my mouth. I didn't have to be told what to do. I set to work licking her succulent twat lips and poking my tongue into her wet woman hole. I licked and nibbled and sucked her clit as she moaned with total pleasure.

Meanwhile, Vince was finger fucking her pussy and asshole. From what little view I had, I saw him go to Janet's night table and take a tube of KY from the drawer. I couldn't actually see what he was doing since Janet had her cunt plastered to my mouth, but by her sounds, I got the feeling that he was using his fingers to work gobs of it into her butthole.

She was yelping, "Oh fuck, Vince. That feels so fucking nasty."

After another few minutes, Janet said, "I think I'm ready."

She moved off my face and then slid down my body to take my cock into her sopping wet slick pussy. She fucked herself on it for a few moments and then said, "Do it Vince. Do it."

Vince positioned himself behind her. Janet let out a bit of a moan and yelp as Vince started pushing his cock into her asshole.

"Relax Honey," he said. "Just relax and let it happen. It's no different than having me in you along with one of those dildoes."

"Not sure Vinny," she moaned. "I'm pretty sure you and Nick are much bigger."

"Just relax and let it happen," Vince cooed. "Just think of how much you've wanted it, thought about it, talked about it, practiced it. I know you want it. YOU know you want it. Let me see how much you really do want it. Relax and let Vinnny wiggle into that backdoor."

Just then, Janet let out a loud moan that was perhaps a mix of pleasure, pain, and victory as Vince's dick penetrated into her ass. I could feel him sliding inside her. It was so weird because it basically felt like Vince was sliding his dick along mine. I knew his dick wasn't actually touching mine, but there was a brief moment of homophobic panic that came over me. I truly never had any fantasies or thoughts of having any sort of sex with a guy. The anxiety passed quickly as Janet continued to fuck herself on both or our cocks.

"OH JESUS! OH FUCKING SHIT! YOU FUCKERS ARE SO DAMNED BIG! TAKE IT EASY." She moaned.

"You're fine Baby," Vince assured her. "You're fine. It's all happening the way you wanted it. Go for it."

Janet put her mouth close to my ear, 'Oh Jesus Nick. It IS really happening. Finally for real. Two honest to God hard cocks in both holes. Oh God, Nick, it's for real this time."

She leaned back up a bit. The look on her face was something I have never forgotten. It was a mix of out-of-body erotic surrender. Her eyes were focused somewhere off in space as though she were looking into another dimension. I could only imagine the female surrender she felt with two hot hard male sex organs deep inside her most secret orifices. There was only one orifice left that could be used to complete the total female penetration trilogy. I'm sure if there was another guy there with us to offer his unit to her mouth, she would have taken it in a heartbeat. I made a promise to myself that if this arrangement with Janet continued for me, I would do my best to set up a foursome to let her have the ultimate total triple penetration experience. I suppose as a man I don't know how most women actually feel about it, but I often imagined that if a woman truly enjoyed having a dick in each of her orifices individually, she had to imagine having them all filled simultaneously. I basically believed that if any man could magically be allowed to be a woman for a day, one of the things he'd want to accomplish as soon as possible would be having three cocks at once.

I was told later in my life that this is not something on a lot of women's bucket list. However, I also think a lot of women wouldn't necessarily want to be honest about admitting it, especially with anyone they may fear would immediately brand her with a scarlet "S" for slut. It might well be like many of those fantasies and secret desires we all have but may assume are too weird to tell others about. Years later I would read some things that made me realize that a lot of those "weird fantasies" and desires are shared by a lot of other people who were also afraid to admit them. Maybe if we could all be honest without fear of judgement, we could all have better sex lives.

As we continued, we fell into and out of rhythms that sometimes had one cock entered while one exited as well as other times where both were entering and exiting at the same time. It was nothing we could plan. We were simply a writhing pile of three humans, two of which had their sex organs in the crotch orifices of another. Janet seemed to have reached a state of being relaxed and stretched enough that she no longer displayed any sort of discomfort or fear. She was going all out to be fucked by two cocks at once. I felt Janet's hand move down between us so that she could finger her clit. Her moans, whimpers, and unintelligible words got louder and more frequent. Finally, she went over the edge into a full screaming orgasm.

"OH FUCKING FUCKING FUCKING SHIT IN FUCKING HEAVEN AND HELL!!! JESUS FUCKING FUCK I'M GONNA FUCKING CUM AND CUM AND CUM!"

I could feel her cunt squeezing and throbbing on my cock and I knew Vince could feel her asshole doing the same. I felt a gush of hot fluid drenching my balls and thighs. I thought that maybe she had lost bladder control and had pissed on me. I had never had this experience with other women. However, I would later learn more from Vince that what I had just experienced was a privilege and not a problem. I fought not to cum because I knew like with Tanya, it was verboten to cum in her cunt.

Finally, Janet collapsed on me. Vince pulled out and then Janet rolled off of me onto her back. Vince immediately straddled her chest and began jerking off with his dick pointed at her face. In seconds he was erupting gobs of his cock lave onto her cheeks and into her open mouth.

As soon as he finished, he said, "Get up her Nicky and give this lady some liquid lunch."

I straddled her face as Vince had done and started jerking off toward her cum covered face. Janet moved my hand away from my dick and said, "Let me suck it. I want to taste my pussy on it."

She took me into her mouth. Rather than make her work so hard, I moved up slightly and started fucking her mouth as I had done earlier. I could see her smile as her eyes looked up and met mine. They seemed to be telling me, "Do it, Nick. Fuck my mouth and feed your man cream to me."

In a moment, I unloaded my pent-up semen into her.

When I was pumped dry, I rolled off to the side opposite from where Vince was positioned. The three of lay there with Janet sandwiched between us in the totally quiet room. Vince was gently stroking Janet's hair while I was slowly stroking her upper arm and shoulder. I was struck with how peaceful and strangely normal it seemed to be lying in this woman's marriage bed after having just fucked her cunt and ass and splattered her face with jizz. It was a bit surreal but over the next year or so, it would become my new normal.

After a long while, I announced, "I have to pee" and got up to go to the bathroom.

"Wait," Janet said getting out of bed. "I need you to do something for me. Vince, get up. Come on. You know what I want."

I really didn't know what Janet had in her mind. I soon I found out and was pretty damned surprised. She got into the tub and said, "I want you guys to shower me."

At first I was too stupid to realize what she meant and was naively ready to turn on the shower when Vince stood by me and began pissing all over Janet's tits and pussy. '

"Not on the face," he said. "Just on her tits and pussy and thighs."

I was more than surprised. I wasn't stupid and realized that some people were into this sort of thing. In fact, one night on liberty, three of my sailor buddies and I were in a French brothel, and one of them paid three women to stand in the tub and piss while we watched. We had already separately fucked them in separate rooms but now my buddy wanted a pee show. However, it wasn't literally onto anybody. Janet introduced me to the next step.

Anyway, at this point, I was in for a penny, in for a pound and I took my que from Vince. I directed my stream onto Janet's tits and belly and pussy. She giggled and giggled saying, "Oooo it feels so nice and warm."

When we were done, I was more surprised at what came next.

"Ok," she said standing up. "Get in here. Now it's your turn."

Vince said to me, "Go with it, Nick. It's not as weird as you may think. It's all just fun."

She positioned us in the tub so that our heads were at opposite ends and our dicks and balls were sort of next to each other. Then she stood over us and showered our respective junk. I have to admit, it was really quite erotic in a nasty, dirty, sinful, kinky way. Janet had just taken my golden shower virginity.